and when I say “for money”, I don’t mean a scenario where we’re all playing for $100 a game… I’m talking more an ideal scenario where everyone has (let’s say) $5 invested, so therefore everyone would have some “skin in the game”.
I’m sure there are all sorts of free sites out there, where as soon as you land on Boardwalk, the other four players hit the little white X on their internet window.
I just find the game interesting and fun to play, and not having the biggest circle of friends in the world, it would be fun to play online against like-minded “competitive” people.
So does such a thing even exist?
I think the only place you can play the official Monopoly™ is on Electronic Arts’ Pogo. There, you can play for Pogo points and win prizes, but I don’t think you’ll find anywhere (legal) that you can bet actual money.
Despite the potential issues with gambling laws, Monopoly is very unsuited for this sort of anonymous play. Two real-life allied players will almost certainly beat anyone except a coalition of three or more allied players.
OP: Have you played games like Dominion or Settlers of Catan? There are big online communities of people who play those games. If you haven’t, try them. In my opinion they are much better games than Monopoly. Even if you don’t agree and prefer Monopoly, they have the advantage of having active player bases. Your second choice game that you actually get to play is probably better than your first choice that’s not available.